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Home , Chlorine, Chlorosarin, HN1 (nitrogen mustard), Lewisite 2, Lewisite 3, QL (chemical)

Schedule 1 Quiz Answer Key

Sarin Reading Molecular Structures in ReadingAugmented Molecular Reality Structures S1-4 in Augmented Reality Atomic Color Code Bonds

Tabun (3) has single, double C: H: S: and triple bonds. Each bond VX type has been circled and la- N: P: As: belled so you know what to look for! Cl: F: O:

Arsenic Arsenic1 1 (H) 1 Single Bond S1-21 (F) Fluorine (F) 3 (C) (O) CarbonFluorine2 (C) (F) 2 Carbon (C)Triple Bond Double Bond (S) 2 (P) Sulfur4 (S) Chlorine4 (Cl) (N) ChlorineSulfur (Cl) (S) 4 DF (Cl)

S1-16 QL

1A(8): Schedule 2 Quiz Answer Key Schedule 3 Quiz Answer Key

S2-18 S2-8 S2-18 S2-8 S3-12 S3-5 (S)-(-)-3-Quinuclidinol (R)-(+)-3-quinuclidinol 2A(1) : Amiton 2A(2) : PFIB O,O-Diethyl S-[2-(diethylamino)ethyl] 1,1,3,3,3-Pentafluoro-2-(tri- S2-13 2B(9) S2-4 phosphorothiolate and corresponding fluromethyl)-1-propene Quinuclidin-3-ol alkylated or protonated 3A(1) : 3A(2) Carbonyl dichloride

S2-16 S2-1 2B(10) S2-16 S2-1 N,N-Dialkyl (Me, Et, n-Pr or i-Pr) aminoethyl-2- and S2-2 corresponding protonated salts S3-12 S3-13 (S)-(+)-3-Quinuclidinyl benzilate* (R)-(-)-3-Quinuclidinyl benzilate* S3-7 2A(3)* : BZ 2-chloro-N,N-dimethylethan-1-amineS2-2 3-Quinuclidinyl benzilate

2-(ethylmethylamino)ethan-1-ol 3A(3) 3A(4) : Hydrogen Trichloronitromethane S2-15 S2-11 S2-9 2B(11) S2-15 S2-11 S2-9 N,N-DialkylS2-10 (Me, Et, n-Pr or i-Pr) aminoethane-2-ols S2-15: Dichloro(methyl)phosphane and corresponding protonated salts Exemptions: N,N-Dimethylaminoethanol and S2-11: Tetrachloro(methyl)phosphane corresponding protonated salts S3-3 S3-14 S2-9: N-[bis(dimethylamino)methylidene]-P-methyl- S2 - 10 N,N-Diethylaminoethanol and corresponding protonated salts phosphonofluoridamidic S2-17 Chemicals, except for those listed in Schedule 1, containing a phosphorus atom to which is bonded one methyl, ethyl or propyl (normal or iso 3B(6) 2B(4) 2B(12) 3B(5) but not further carbon atoms. (Exemption: Fonofos = O-Ethyl S-phenyl ethylphosphosphonate) N,N-Dialkyl (Me, Et, n-Pr or i-Pr) Phosphorus oxychloride aminoethane-2-thiols S2-17S2-17 and corresponding protonated salts

2-(dimethylamino)ethan-1-thiol S3-11 S3-9 S2-3 S2-6

Thiodiglycol: 2B(13) S2-14 3B(7) 2B(5) 2B(6) Bis(2-hydroxyethyl)sulfide 3B(8) Trimethyl phosphite N,N-Dialkyl (Me, Et, n-Pr or i-Pr) Dialkyl (Me, Et, n-Pr or i-Pr) N,N-dialkyl phosphoramidic dihalides (Me, Et, n-Pr or i-Pr) phosphoramidates

S2-7 Pinacolyl : 2B(14) S2-5 3,3-Dimethylbutan-2-ol S3-17 S3-1 S2-12

S3-16 3B(9) 3B(10) 3B(15) Triethyl phosphite Dimethyl phosphite 2B(8) 2B(7) Ethyldiethanolamine 2,2-Diphenyl-2-hydroxyacetic acid

S3-10 S3-6 S3-6 S3-15 S3-2 S3-8 S3-4 S3-10 S3-6 S3S3-15-15 S3-2S3-2 3B(11) 3B(12) 3B(13) 3B(14) 3B(16) 3B(17) Diethyl phosphite Sulfur monochloride Sulfur dichloride Methyldiethanolamine Triethanolamine Scheduled Chemicals under the Chemical Weapons Convention (CWC)

Schedule 1 Schedule 2 Schedule 3

Guidelines for Schedule 1 Guidelines for Schedule 2 Guidelines for Schedule 3 The following criteria shall be taken into account in considering whether a toxic The following criteria shall be taken into account in considering whether a toxic The following criteria shall be taken into account in considering whether a toxic chemical or precursor should be included in Schedule 1: chemical not listed in Schedule 1 or a precursor to a Schedule 1 chemical or to a chemical or precursor, not listed in other Schedules, should be included in (a) It has been developed, produced, stockpiled or used as a as chemical listed in Schedule 2, part A, should be included in Schedule 2: Schedule 3: defined in Article II; (a) It poses a significant risk to the object and purpose of this Convention because (a) It has been produced, stockpiled or used as a chemical weapon; (b) It poses otherwise a high risk to the object and purpose of this Convention by it possesses such lethal or incapacitating toxicity as well as other properties (b) It poses otherwise a risk to the object and purpose of this Convention because it virtue of its high potential for use in activities prohibited under this that could enable it to be used as a chemical weapon; possesses such lethal or incapacitating toxicity as well as other properties that Convention because one or more of the following conditions are met: (b) It may be used as a precursor in one of the chemical reactions at the final stage might enable it to be used as a chemical weapon; (i) It possesses a chemical structure closely related to that of other toxic of formation of a chemical listed in Schedule 1 or Schedule 2, part A; (c) It poses a risk to the object and purpose of this Convention by virtue of its chemicals listed in Schedule 1, and has, or can be expected to have, (c) It poses a significant risk to the object and purpose of this Convention by importance in the production of one or more chemicals listed in Schedule 1 or comparableproperties; virtue of its importance in the production of a chemical listed in Schedule 1 or Schedule 2, part B; (ii) It possesses such lethal or incapacitating toxicity as well as other Schedule 2, part A; (d) It may be produced in large commercial quantities for purposes not properties that would enable it to be used as a chemical weapon; (d) It is not produced in large commercial quantities for purposes not prohibited prohibited under this Convention. (iii) It may be used as a precursor in the final single technological stage of under this Convention. Schedule 3 Part A, Toxic Chemicals production of a toxic chemical listed in Schedule 1, regardless of O Schedule 2 Part A, Toxic Chemicals O + whether this stage takes place in facilities, in munitions or elsewhere; Cl N O F O- (c) It has little or no use for purposes not prohibited under this Convention. S F F Cl N P Cl Cl N Cl N C H Cl O Phosgene: Carbonyl dichloride Chloropicrin: Trichloronitromethane O

R4 Schedule 1 Part A, Toxic Chemicals O 3A(1) 3A(2) 3A(3) O F F O 3A(4)

P

O R3 OH OH

OR OR CH3 2 O 2 Including corresponding F O Schedule 3 Part B, Precursors P R3 S N O alkylated and/or F F N N R O Cl CH3 1 R1 P N protonated salts F S Cl Cl O O C Cl Cl Amiton PFIB (R)-(-)-3-Quinuclidinyl benzilate (S)-(+)-3-Quinuclidinyl benzilate Cl R1= Me, Et, n-Pr, i-Pr Cl P Cl R1= Me, Et, n-Pr, i-Pr N O R1 P R =C -C incl. cycloalkyl 2A(1) R =C -C incl. cycloalkyl 2 1 10 2-Chloroethylchloromethylsulfide 2A(2) 2A(3)* P H3C P CH3 P 2 1 10 R2 R =Me, Et, n-Pr, i-Pr Cl e.g. , 3 Cl Cl Cl Cl O O H C O O CH R =Me, Et, n-Pr, i-Pr 3 3 R1= Me, Et, n-Pr, i-Pr 4 1A(1) e.g. VX agent S Phosphorus Phosphorus trichloride Phosphorus pentachloride Trimethyl phosphite Triethyl phosphite R2= C1-C10 incl. cycloalkyl Schedule 2 Part B, Precursors Including corresponding Cl Cl O R3= Me, Et, n-Pr, i-Pr oxychloride 3B(6) 3B(7) 3B(8) 3B(9) alkylated and/or S R O e.g. Tabun Mustard : Bis(2-chloroethyl)sulfide X X X 3 3B(5) protonated salts 1 1 1 1A(2) X R P R1 2 P N P O 1A(3) S S R P R P P X2 N R1 O O Cl X O S X Cl Cl X3 2 1 R X X X R 4 O R O Bis(2-chloroethylthio) 4 2 3 2 2 H C P CH P As 3 3 N R =Me, Et, n-Pr, i-Pr R , R =Me, Et, n-Pr, i-Pr 1 2 O O H3C O O CH3 Cl S S S Cl Cl Cl Cl X - X =Any group not attached to X , X = R , R ,R ,R =Me, Et, n-Pr, i-Pr S Cl 1 4 1 2 1 2 3 4 H H S Cl Cl Cl Cl Cl 1: 2-Chlorovinyldichloroarsine HN1: Bis(2-chloroethyl)ethylamine Cl S the phosphorus atom through a carbon Exemption: Fonofos Dimethyl phosphite Diethyl phosphite Sulfur monochloride Sulfur dichloride Thionyl chloride Cl :1,2-Bis(2-chloroethylthio) 2B(5) 2B(6) 2B(4) 3B(10) 3B(11) 3B(12) 3B(13) 3B(14)

As N S S Cl Cl Cl Cl OH Cl Cl : Bis(2-chlorovinyl)chloroarsine HN2: Bis(2-chloroethyl)methylamine 1,3-Bis(2-chloroethylthio)-n-propane H3C Cl OH HO R2 Cl HO CH3 Cl S Cl OH N Cl S N N N Cl R As 1 HO OH HO OH HO OH 1,4-Bis(2-chloroethylthio)-n-butane N N Cl Cl O Ethyldiethanolamine Methyldiethanolamine Triethanolamine As N R1, R2 = Me, Et, n-Pr, i-Pr S S Cl Cl Cl Cl Including corresponding 3B(15) 3B(16) 3B(17) Cl Cl Arsenic Trichloride 2,2-Diphenyl-2-hydroxyacetic acid (S)-(+)-3-Quinuclidinol (R)-(-)-3-Quinuclidinol protonated salts : Tris(2-chlorovinyl) HN3: Tris(2-chloroethyl)amine 1,5-Bis(2-chloroethylthio)-n-pentane 2B(7) 2B(8) 2B(9) 2B(10) Lewisites Nitrogen mustards S O S 1A(5) 1A(6) R

Cl Cl 2 O Bis(2-chloroethylthiomethyl)ether N R1 OH OH H2N H HO R1 N N NH S S O 2 R , R =Me, Et, n-Pr, i-Pr HS R HN Cl O Cl 1 2 2 S N Including corresponding R , R =Me, Et, n-Pr, i-Pr O-Mustard: Bis(2-chloroethylthioethyl)ether 1 2 HO OH N OH protonated salts Including corresponding HN OH Exemptions: R1= R2= Me protonated salts Thiodiglycol: Bis(2-hydroxyethyl)sulfide (S)-(+)- (R)-(-)-Pinacolyl alcohol Sulfur mustards R1= R2= Et Ricin 1A(4) 2B(11) 2B(12) 2B(13) 2B(14) 1A(7) 1A(8)

Schedule 1 Part B, Precursors Cl R R O 3 4 P Schedule 3 Cl O O (Used in production of Schedule 1 chemicals) N P R2 P R1 P F R1 O O O O O

F R1= Me, Et, n-Pr, i-Pr Including corresponding

R2= C10 incl. cycloalkyl alkylated and/or R1= Me, Et, n-Pr, i-Pr R3= Me, Et, n-Pr, i-Pr protonated salts S e.g. DF R4= Me, Et, n-Pr, i-Pr e.g. QL Schedule 2 Cl Cl Schedule 1 1B(9) 1B(10) 1B(11) 1B(12) (A Precursor) Thionyl chloride 3B(14) ORGANISATION FOR THE S S HO OH Cl Cl PROHIBITION OF CHEMICAL WEAPONS Thiodiglycol Sulfur mustard Working Together for a World Free of Chemical Weapons 2B(13) 1A(4)

@opcw Scheduled chemicals, including those in schedules 1 and 2, can have scientifically and economically /opcwonline /opcwonline @opcw_st /company/opcw /opcw Relationship between Schedules, illustrated with sulfur mustard. important uses. This chart captures the number of yearly scientific publications that refer to them.