[ CAS No. 127-65-1 ] {[proInfo.proName]}

Name: 127-65-1|Sodium chloro(tosyl)amide|98%
Brand: Ambeed
SKU: A663166
Rating: 95 (40 reviews)

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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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Structure of 127-65-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 127-65-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 127-65-1 ]

SDS Specification

Alternatived Products of [ 127-65-1 ]

Product Details of [ 127-65-1 ]

CAS No. :	127-65-1	MDL No. :	MFCD00000522
Formula :	C₇H₇ClNNaO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VDQQXEISLMTGAB-UHFFFAOYSA-N
M.W :	227.64	Pubchem ID :	3641960
Synonyms :		Chemical Name :	Sodium chloro(tosyl)amide

Calculated chemistry of [ 127-65-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.33
TPSA :	45.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.04
Log Po/w (WLOGP) :	2.68
Log Po/w (MLOGP) :	0.97
Log Po/w (SILICOS-IT) :	-0.68
Consensus Log Po/w :	1.0

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.75
Solubility :	0.408 mg/ml ; 0.00179 mol/l
Class :	Soluble
Log S (Ali) :	-2.63
Solubility :	0.535 mg/ml ; 0.00235 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.75
Solubility :	0.41 mg/ml ; 0.0018 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.24

Safety of [ 127-65-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P273-P280-P284-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P342+P311-P363-P405-P501	UN#:	3263
Hazard Statements:	H302-H314-H334-H412	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 127-65-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 127-65-1 ]
Downstream synthetic route of [ 127-65-1 ]

[ 127-65-1 ] Synthesis Path-Upstream 1~16

1
[ 18438-38-5 ]
[ 127-65-1 ]
[ 21948-75-4 ]
[ 76468-92-3 ]

Reference： [1] Phosphorus and Sulfur and the Related Elements, 1983, vol. 16, p. 167 - 180

2
[ 127-65-1 ]
[ 100-52-7 ]
[ 63160-12-3 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 12, p. 4894 - 4904

3
[ 127-65-1 ]
[ 106-53-6 ]
[ 98-58-8 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

4
[ 127-65-1 ]
[ 1849-36-1 ]
[ 98-74-8 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

5
[ 36801-01-1 ]
[ 127-65-1 ]
[ 49584-26-1 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

6
[ 127-65-1 ]
[ 4892-02-8 ]
[ 26638-43-7 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

7
[ 371-42-6 ]
[ 127-65-1 ]
[ 349-88-2 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

8
[ 3814-20-8 ]
[ 127-65-1 ]
[ 1788-10-9 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

9
[ 825-83-2 ]
[ 127-65-1 ]
[ 2991-42-6 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

10
[ 127-65-1 ]
[ 3930-83-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrogenchloride In sodium hydroxide; diethyl ether	EXAMPLE 2 [¹²⁵ ](R)-N-[(1-Ethyl-2-pyrrolidinyl)-5-iodo-2-methoxybenzamide A solution of (R)-N-[(1-ethyl-2-pyrrolidinyl)methyl[-2-methoxy-5-tri-n-butyltinbenzamide (15 μg, 22 nmol) in diethylether (10 μL) was mixed with 10.4 mCi of Na¹²⁵ I (3.2 μg, 22 nmol) in 0.001N NaOH (29 μL). Hydrochloric acid (0.1N, 10 μL) was added followed by the addition of an aqueous solution (5 μL) of sodium N-chloro-4-methylbenzene sulfonamide (16 μg, 70 nmol). After 10 min. at 20° C., NaOH (2N, 20 μL) was added. Extraction with ether (2*150 μL) gave 7.2 mCi of the desired iodobenzamide. Specific activity 590 Ci/mmol, radiochemical yield 70percent.

Reference： [1] Patent: US5154913, 1992, A,

11
[ 7647-01-0 ]
[ 103-88-8 ]
[ 127-65-1 ]
[ 3460-23-9 ]

Reference： [1] Journal of the Chemical Society, 1923, vol. 123, p. 3394

12
[ 6302-65-4 ]
[ 127-65-1 ]
[ 69812-51-7 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

13
[ 70-55-3 ]
[ 127-65-1 ]

Reference： [1] Synthesis, 2009, # 16, p. 2797 - 2801
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2004, vol. 59, # 1, p. 63 - 72
[3] International Journal of Chemical Kinetics, 2005, vol. 37, # 9, p. 572 - 582

14
[ 473-34-7 ]
[ 70-55-3 ]
[ 127-65-1 ]

Reference： [1] International Journal of Chemical Kinetics, 1995, vol. 27, # 7, p. 663 - 674

15
[ 91358-96-2 ]
[ 127-65-1 ]
[ 85822-16-8 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057

16
[ 6636-78-8 ]
[ 127-65-1 ]
[ 185220-68-2 ]

Reference： [1] Patent: US2004/53908, 2004, A1,

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Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid In methanol at 20℃; for 1h;	Step 1. Synthesis of N-(diphenyl-λ4-sulfanylidene)-4-methylbenzenesulfonamide Diphenyl sulfi de (9 mL, 50 mmol) wasadded to a solution of chloramine T (15.49 g, 55 mmol) in MeOH(70 mL). Then a solution of AcOH (2.5 mL) in MeOH (12.5 mL)was added dropwise. The mixture was stirred for 1 h at roomtemperature and then poured into a cold solution of NaOH (2.5 g)in water (225 mL). The white precipitate that formed was fi lteredoff , washed with water, and dried in air. The product was recrystallizedfrom MeOH. Yield 16.14 g (91%), m.p. 112-113 °C(cf. lit. data23: m.p. 113 °C, cf. lit. data34: 123-124 °C).
86%	In acetonitrile at 20℃; for 16h;
80%	In acetonitrile at 80℃; for 3h;

6%	In dichloromethane
	With N-benzyl-N,N,N-triethylammonium chloride
	In water Heating;

Yield	Reaction Conditions	Operation in experiment
95%	In acetonitrile at 20℃; for 16h;
	In water Heating;
	In acetonitrile

Yield	Reaction Conditions	Operation in experiment
75%	With mesoporous silica MCM-41; iodine; potassium carbonate In water at 20℃; for 3h;
65%	With iodine In acetonitrile for 10h; Ambient temperature; neutral buffer, pH 6.86;
53%	With silver nitrate In benzene at 60℃; for 8h;

[ CAS No. 127-65-1 ] {[proInfo.proName]}

Quality Control of [ 127-65-1 ]

Related Doc. of [ 127-65-1 ]

Product Details of [ 127-65-1 ]

Calculated chemistry of [ 127-65-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 127-65-1 ]

Application In Synthesis of [ 127-65-1 ]

[ 127-65-1 ] Synthesis Path-Upstream 1~16

[ 127-65-1 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

46.3%	With tetra-(n-butyl)ammonium iodide In water at 20℃; for 48h;
34%	With iodine In acetonitrile at 20℃; for 24h;
67 % Spectr.	With 5A molecular sieve In acetonitrile at 25℃; for 3h;
	With iodine In acetonitrile at 20℃; for 24h; Schlenk technique;

Yield	Reaction Conditions	Operation in experiment
94%	With phenyltrimethylammonium tribromide In acetonitrile at 25℃; for 12h;
78%	With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 16h;
66%	With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 16h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
54%	With phenyltrimethylammonium tribromide In acetonitrile at 25℃; for 12h;
42%	With pyridinium perbromide hydrobromide In acetonitrile at 25℃; for 12h;
	With N-benzyl-N,N,N-triethylammonium chloride; iodine In dichloromethane; water at 26℃; for 24h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
97%	With phenyltrimethylammonium tribromide In acetonitrile at 25℃; for 12h;
79%	With iodine; Aliquat 336 at 20℃; for 3h;
66%	With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 16h; Inert atmosphere;

58%	With iodine; silica gel; potassium carbonate In water at 20℃; for 3h;
	With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 12h;

Yield	Reaction Conditions	Operation in experiment
98%	With potassium dioxotetrahydroxoosmate(VI); sodium hydrogencarbonate In water for 6h;
96%

Yield	Reaction Conditions	Operation in experiment
64%	With phenyltrimethylammonium tribromide In acetonitrile at 28℃; for 12h;
64%	With trimethylphenylammonium tribromide In water; acetonitrile at 28℃; for 12h;	4.1. General procedure for sharpless aziridination General procedure: To a mixture of an appropriate olefin (3 mmol) and TsNClNa*3H2O (CAT) (0.930 g, 3.3 mmol) in CH3CN (15 mL), was added phenyltrimethylammonium tribromide, (PTAB) (0.113 g, 0.3 mmol) at 28 °C. After 12 h of vigorous stirring, the reaction mixture was concentrated and filtered through a short column of silica gel and eluted with 10% EtOAc in hexanes. After evaporation of solvent, the resultant solid was purified by flash column chromatography to yield the corresponding aziridines in good yield.

Yield	Reaction Conditions	Operation in experiment
64%	With 4 A molecular sieve In acetonitrile at 65 - 70℃; for 15h;
62%	With tetrakis(actonitrile)copper(I) hexafluorophosphate; C₂₀H₁₈N₆O₈ In toluene; acetonitrile at 20℃; Molecular sieve; Inert atmosphere; Reflux; regioselective reaction;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 70 percent / acetic acid / ethanol / 1 h / 20 °C 2: 68 percent / Zn-Cu / tetrahydrofuran / 0.33 h / 20 °C 3: 88 percent / zinc; acetic acid; TMEDA / ethanol / 1 h / 20 °C 4: 83 percent / BH₃*THF / tetrahydrofuran / 20 h
	Multi-step reaction with 4 steps 1: 70 percent / AcOH / ethanol / 1 h / 20 °C 2: 68 percent / Zn-Cu / tetrahydrofuran / 0.33 h / 20 °C 3: 88 percent / Zn; AcOH; TEMDA / ethanol / 1 h / 20 °C 4: 83 percent / BH₃ / tetrahydrofuran / 20 h / 0 °C

Yield	Reaction Conditions	Operation in experiment
79%	In toluene at 80℃; for 2h;	13.2 Step 2: N-tosylmethanesulfonimidoyl Chloride 13c The compound 208 chloramine T (1.5 g, 6.7 mmol) was added to 209 toluene (50 mL). The mixture was heated to reflux for 5 hours, while water was removed by a water separator. The mixture was cooled to room temperature. 206 Methanesulfinic chloride 9 1b (1 g, 10 mmol) was added to the reaction solution. The mixture was heated to 80° C. for 2 hours. After cooling to room temperature, the solid was removed. The reaction solution was concentrated in vacuo to obtain 210 N-tosylmethanesulfonimidoyl chloride 13c (1.5 g), yield 79%. (0236) 1H NMR (400 MHz, CDCl3, ppm): δ 7.88 (d, 2H), 7.33 (d, 2H), 3.78 (s, 3H), 2.45 (s, 3H).
	In toluene at 0 - 80℃; for 2h;	1.2 Synthesis of 3: (Step 1 & 2) Dimethyldisulfide 1 (5 g, 53 mmol) and acetic acid (6 mL, 106 mmol) weremixed under nitrogen atmosphere and cooled to- 20 °C. Sulfuryl chloride (13 mL, 159 mmol)was added dropwise with stirring. The mixture was then stirred for 1 hour at -20 °C andafterwards allowed to come to room temperature and continued for another two hours. Acetylchloride was distilled off from the reaction mixture. Crude methanesulfinyl chloride 2 obtained20 was used in the next step without further purification. To a solution of chloramine T (14.95 g, 53 mmol) in dry toluene (220 mL) wasadded a solution ofmethanesulfinyl chloride 2 (5.2 g, 53 mmol) in dry toluene (10 mL) at 0 °C.The resulting suspension was heated at 80 oc for 2 hours with stirring. After cooling, the solidwas filtered off and washed with dry toluene (1 00 mL ). The filtrate was evaporated in vacuo and25 the crude mixture was purified through silica gel chromatography to obtain 3 as off white solid. 1H NMR (300 MHz, CDCh): o 7.85- 7.91 (m, J = 8.42 Hz, 2H), 7.31- 7.38 (m, J = 8.23 Hz,2H), 3.78 (s, 3H), 2.45 (s, 3H).
	In toluene at 85℃; for 2h; Inert atmosphere;	A.3 Scheme A Step 3: To a stirred solution of Chloramine-T (38.8 g, 81.6 mmol) in dry toluene (180 mL) at 20°C was added a solution of A4 (8 g, 138.0 mmol) in dry toluene (20 mL). The reaction mixture was heated at 85°C for 2 h under a nitrogen atmosphere. After cooling, the solid was filtered off and the residue washed with dry toluene. The filtrate was evaporated in vacuo to yield the sulfonimidoyl chloride A5 which was taken to the next step without further purification.

Yield	Reaction Conditions	Operation in experiment
67%	With ethanol; potassium <i>tert</i>-butylate; copper diacetate at 20℃; for 12h;	III. General experimental procedure for the reaction of chloramine T and arylboronic acid General procedure: A test tube with stir bar was charged with N-Chloro-N-sodiosulfonamide 2 (0.3 mmol), arylboronic acid 1 (0.36 mmol) and tBuOK (50.5 mg, 0.45 mmol). A solution of Cu(OAc)2 (2.7 mg,0.015 mmol) in EtOH (1.5 mL) was then added to the test tube. The reaction mixture was stirred under air at room temperature for 12 h, then the heterogeneous mixture was diluted with ethylacetate. The resulting mixture was directly filtered through a pad of silica gel, then the silica gelwas eluted with ethyl acetate. The organic solutions was combined, and the solvent was removedunder reduced pressure. The crude product was purified by silica-gel column chromatography toafford the desired product.
61%	With copper(l) iodide; potassium carbonate In water at 20℃; for 18h;

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
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P335	Brush off loose particles from skin.
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
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