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2-Bromothiazole

2-Bromothiazole structure

CAS No:
3034-53-5
Formula:
C3H2BrNS
Chemical Name:
2-Bromothiazole
Synonyms:
Thiazole,2-bromo-;2-Bromothiazole;2-Bromo-1,3-thiazole;NSC 91532
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Colourless Liquid

2-Bromothiazole Basic Attributes

Molecular Weight：

164.02

Exact Mass：

164.02

EC Number：

221-229-4

NSC Number：

91532

DSSTox ID：

DTXSID9062805

HScode：

2934100090

Characteristics

PSA：

41.1

XLogP3：

1.8

Appearance：

Appearance colorless clear liquid

Density：

1.9±0.1 g/cm3

Melting Point：

39.5 °C

Boiling Point：

171 °C

Flash Point：

63.3±0.0 °C

Refractive Index：

1.605

Water Solubility：

H2O: insoluble

Storage Conditions：

2-8ºC

Safety Information

Transport codes：

1993

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S23-S24/25

Marks：

Xi: Irritant;F: Flammable;

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 8 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-Bromothiazole Use and Manufacturing

Methods of Manufacturing

2-Amino-thiazol 0.25mol 150ml45percent sulfuric acid was dissolved in 500ml reaction flask and stirred to dissolve 2-aminothiazol-section and cooled to 2 , 50ml of concentrated nitric acid 65percent was added dropwise, maintaining the internal temperature should not exceed 10 . Then 50ml solution of sodium nitrite was slowly dropped 5mol / l, the addition was completed, stirring was continued for 1h, controlling the temperature below 7 . The reaction was continued with a dropping funnel, the red-brown diazonium salt solution was added dropwise 200ml solution containing 74g of sodium bromide and 40g copper sulfate carried bromination, maintained at 6 , dropping time of about 1.5h, after the addition was complete 7H, N2 so excluded; after cooling the solution was added 20percent NaOH and the solution was adjusted pH of 6 to 7, then washed with water steam distillation to collect the aqueous solution containing the 2-bromothiazole, dried over MgSO4 solution by distillation, vacuum distillation collect bp71 ~ 73 / 2.4kPa fraction, 2-bromothiazole 35.2g, a yield of 85.8percent, showing that the reaction temperature is maintained at the present application 0 ~ 10 , the reaction rate is faster, while also reducing side reactions, the reaction yield has been greatly improved.To a cool solution of thiazol-2-amine (5.0 g, 50 mmol) in 85percent H3P04 was added conc. nitricacid and stirred the reaction mixture for iO mins followed by addition of aq.NaNO2 (4. i4 g, 60 mmol), continued stirring for i h at 0°C.Then added aq.Cu504 (6.36 g, 40 mmol) & NaBr(i4.49 g, i45 mmol).The reaction mass was further stirred at 0°C for 6 h then at ft for i6 h.The reaction mass was basified with KOH & Na2CO3 up to pH-9 and extracted with DCM.The organic layers were separated and concentrated to afford 2.5 g of title compound . ‘HNMR (300 MHz, DMSO-d6): 7.62-7.6i (d, J = 3.0 Hz, iH), 7.3 i-7.30 (d, J = 3.3 Hz, iH)

Uses

Aryl halide used to N-arylate 5- and 7-azaindoles.1 Copper-catalyzed cyanation provides 2-cyanothiazole.2 2-Bromothiazole is a heterocyclic S compound to induce base-pair substitution and having mutagenic activity.

Manufacturing Info：

Thiazole, 2-bromo-: ACTIVE

Computed Properties

Molecular Weight:164.03
XLogP3:1.8
Hydrogen Bond Acceptor Count:2
Exact Mass:162.90913
Monoisotopic Mass:162.90913
Topological Polar Surface Area:41.1
Heavy Atom Count:6
Complexity:50.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Phosphonic acid

Phosphoric acid

Nitric acid

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