598-78-7

Basic information

• Product Name: 2-Chloropropionic acid
• Synonyms: ALPHA-CHLOROPROPIONIC ACID;(±)-2-Chloropropionicacid,97%;A-CHLOROPROPIONIC ACID;Propanoic acid, 2-chloro-;(n)-2-chloropropionic acid;MONO-CHLOROPROPANOICACID;2-Chlorpropionsure;2-CHLOROPROPIONIC ACID (92%)
• CAS NO: 598-78-7
• Molecular Formula: C₃H₅ClO₂
• Molecular Weight: 108.52
• EINECS: 209-952-3
• Product Categories: Organic acids;C1 to C5;Carbonyl Compounds;Carboxylic Acids;API Intermediate
• Mol File: 598-78-7.mol
• Article Data: 21

Chemical Properties

• Melting Point: -12--14 °C
• Boiling Point: 170-190 °C(lit.)
• Flash Point: 215 °F
• Appearance: colourless liquid
• Density: 1.182 g/mL at 25 °C(lit.)
• Vapor Pressure: 4 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.4345(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: soluble
• PKA: 2.96±0.10(Predicted)
• Water Solubility: freely soluble
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1720259
• CAS DataBase Reference: 2-Chloropropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropropionic acid(598-78-7)
• EPA Substance Registry System: 2-Chloropropionic acid(598-78-7)

Safety Data

• Hazard Codes: C
• Statements: 22-35-21/22
• Safety Statements: 23-26-28-36-45-36/37/39-28A
• RIDADR: UN 2511 8/PG 3
• WGK Germany: 1
• RTECS: UE8575000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 598-78-7(Hazardous Substances Data)

Usage

Description

2-Chloropropionic acid is a colorless to white crystalline solid or liquid that is denser than water; therefore, can sink and mix with water. It has a slight odor and is the simplest chiral chlorocarboxylic aid.

Preparation

2-Chloropropionic acid is prepared from diazotization of L-alanine in hydrochloric acid.

Application

2-Chloropropionic acid is employed in the production of propargyl 2-chloropropionate (PCP), which is an atom transfer radical polymerization (ATRP) initiator, by the esterification of propargyl alcohol. The chemical is also used in the synthesis of benzimidazole derivatives when treated with o-phenylenediamine phosphate. It can also be used in the preparation of biologically active chitin derivative (1-carboxyethyl) chitosan. It is used as a building block for the preparation of herbicides, dyestuffs, pesticides, as well as forestand agro-chemicals.

Biochemical Action

2-Chloropropionic acid induces necrosis of granule cell layer of rat cerebellum when administered orally.

Safety

2-Chloropropionic acid is a neurotoxin, as such it should be handled with utmost care. When inhaled, the chemical can irritate the nose, throat, and lungs, causing wheezing and coughing. The chemical is a corrosive substance, which may occur by ingestion. Contact of the chemical with the eyes and skin may cause pain, irritation, redness, and severe burns.

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 598-78-7 differently. You can refer to the following data:
1. Intermediate for weed killers.
2. 2-Chloropropionic acid is used in the preparation of propargyl 2-chloropropionate (PCP), an atom transfer radical polymerization (ATRP) initiator, by the esterification of propargyl alcohol.It can be employed in the synthesis of a biologically active chitin derivative, (1-carboxyethyl) chitosan.It can be treated with o-phenylenediamine phosphate to synthesize benzimidazole derivatives.

General Description

A pale liquid with a slight odor. Sinks in and mixes with water. Only aluminum, stainless steel or steel covered with a protective lining or coating may contact the liquid or vapor.

Air & Water Reactions

Water soluble.

Reactivity Profile

2-Chloropropionic acid is neutralized in exothermic reactions by all bases. Reacts with aqueous solutions containing a chemical base and dissolves if neutralization generates a soluble salt. May react with active metals to form gaseous hydrogen and a metal salt. May corrode or dissolve iron, steel, and aluminum parts and containers. Reacts with cyanide salts to generate gaseous hydrogen cyanide. Reacts with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides to generate flammable and/or toxic gases and heat. Reacts with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide) but some heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. May initiate polymerization reactions or catalyze other chemical reactions. Fire produces highly toxic chloride fumes [USCG, 1999].

Hazard

Combustible. Toxic by skin contact. Male reproductive damage.

Health Hazard

Harmful if inhaled. Irritating to throat. May cause severe skin and eye burns. Harmful if absorbed through skin.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

2-Chloropropionic acid on oral administration induces necrosis of granule cell layer of rat cerebellum.

Safety Profile

Poison by skin contact. A corrosive. Combustible when exposed to heat or flame. To fight fire, use water, foam, alcohol foam. When heated to decomposition it emits toxic fumes of Cl-. See also 3-CHLOROPROPIONIC ACID.

Purification Methods

Dry it with P2O5 and fractionally distil it under vacuum. [Beilstein 2 IV 745.]

InChI:InChI=1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m0/s1

Synthetic route

1-chloroethyl phenyl sulfoxide (26910-40-7) + carbon dioxide (124-38-9) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
Stage #1: 1-chloroethyl phenyl sulfoxide With cyclohexylmagnesiumchloride In tetrahydrofuran; toluene at -78℃; for 0.166667h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; toluene at -78℃; for 3h;	100%

2-chloropropanal (683-50-1) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;	99%
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	97%
With sodium chlorite; sodium dihydrogenphosphate In water; tert-butyl alcohol for 1.5h;

propionic acid (802294-64-0) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With sulfuric acid; chlorine; propionic acid anhydride at 130℃; under 760.051 Torr; for 3h; Time;	97.22%
Stage #1: propionic acid With phosphorus trichloride at 160℃; Stage #2: With trichloroisocyanuric acid at 160℃;	76%
Chlorierung;

2-Chloroacrylic acid (598-79-8) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With phenylsilane; C12H23N2O2P In tetrahydrofuran at 23℃; for 2h;	91%

2-chloro-1-propanol (78-89-7) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With potassium phosphate; carbon dioxide; CrH6Mo6O24(3-)*3H3N*3H(1+) In dimethyl sulfoxide at 80℃; under 750.075 Torr; for 24h; Green chemistry;	87%

rac-Ala-OH (302-72-7) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With pyridinium polyhydrogen fluoride; potassium chloride; sodium nitrite for 72h; Ambient temperature;	74%
With nitric acid folgendes Erwaermen mit konz.HCl;

propionic acid (802294-64-0) → 2,2-Dichloropropionic acid (75-99-0) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With chlorine; pyrographite; propionic acid anhydride at 130℃; under 760.051 Torr; for 2.5h;	A 10.47% B 68.23%

2-Chloro-2-(toluene-4-sulfinyl)-propionic acid (148586-45-2) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With ethylmagnesium bromide In tetrahydrofuran at -78℃; for 0.166667h;	67%
With ethylmagnesium bromide; water; ammonium chloride 1.) THF, -78 deg C, 10 min; Yield given. Multistep reaction;

propionic acid (802294-64-0) → 3-Bromopropionic acid (590-92-1) + chloropropionic acid (107-94-8) + 2-Bromopropionic acid (598-72-1) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With hydrogenchloride; oxygen; potassium bromide; sodium nitrite In chloroform; water at 40℃; under 760.051 Torr; for 18h; Sealed tube; Irradiation;	A 65% B n/a C 23% D n/a

2-chlorpropionitrile (1617-17-0) → 2-Chloropropionamide (27816-36-0) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
at 30℃; for 1.5h; Rhodococcus sp. (SP 361), pH 7;	A 8% B 43%

LACTIC ACID (849585-22-4) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With phosphorus pentachloride Behandeln des α-Chlorpropionsaeurechlorids mit Wasser;

2-hydroxy-1-nitropropane (3156-73-8) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With hydrogenchloride at 140℃;

propionyl chloride (79-03-8) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With phosphorus at 105 - 110℃;
With phosphonic Acid at 100 - 120℃;

3-chloro-2-butanone (4091-39-8) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With nitric acid; (R,S)-2-chloropropionic acid unter Durchleiten von Luft bei 90grad;

propionic acid (802294-64-0) → chloropropionic acid (107-94-8) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With chlorine Irradiation.im UV-Licht;
With hydrogenchloride Electrolysis.an einer Platinanode;
With hydrogenchloride Electrolysis.an Platinanode;

propionic acid (802294-64-0) → chloropropionic acid (107-94-8) + 2,3-dichloropropanoic acid (565-64-0) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
beim Chlorieren in der fluessigen Phase unter Belichtung;

propionic acid (802294-64-0) → cyclic anhydride of β-sulfopropionic acid (5961-88-6) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With sulfuryl dichloride Irradiation.Gluehlampenlicht;

1-Nitropropen (3156-70-5) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With hydrogenchloride at 20 - 40℃;

1,3-dichlorobutan-2-one (16714-77-5) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With sodium hypobromide

2-hydroxy-propionitrile (78-97-7) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
With phosphorus pentachloride Verseifen des entstandenen α-Chlor-propionitrils durch Erhitzen mit konz.Salzsaeure;

chlorosulfonic acid (7790-94-5) + propionic acid (802294-64-0) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
at 90 - 120℃; beim Chlorieren;

propionic acid (802294-64-0) + phosphorus trichloride (7719-12-2, 52843-90-0) → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
at 90 - 120℃; beim Chlorieren;

propionyl chloride (79-03-8) + propionic acid (802294-64-0) + H3PO3 → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
at 90 - 120℃; beim Chlorieren;

1,3-dichlorobutan-2-one (16714-77-5) + NaOBr → (R,S)-2-chloropropionic acid (598-78-7)

propionic acid (802294-64-0) + red phosphorus → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
at 105 - 110℃; beim Chlorieren;

propionic acid (802294-64-0) + S2cl2 → (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
at 90 - 120℃; beim Chlorieren;

hydrogenchloride (7647-01-0) + propionic acid (802294-64-0) → chloropropionic acid (107-94-8) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
Electrolysis;

chlorine (7782-50-5) + propionic acid (802294-64-0) → chloropropionic acid (107-94-8) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
im UV-Licht(λ:350-400nm);

tetrachloromethane (56-23-5) + chlorine (7782-50-5) + propionic acid (802294-64-0) → chloropropionic acid (107-94-8) + (R,S)-2-chloropropionic acid (598-78-7)

Conditions	Yield
im UV-Licht(λ:350-400nm);

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + (R,S)-2-chloropropionic acid (598-78-7) → diclofop (40843-25-2)

Conditions	Yield
With sodium hydroxide; phosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene; water	99.5%

trans-2-(naphthalen-2-yloxy)cyclohexan-1-ol + (R,S)-2-chloropropionic acid (598-78-7) → (1R,2R)-2-(naphthalen-2-yloxy)cyclohexyl (S)-2-chloropropanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; diastereoselective reaction;	99%

camptothecin (7689-03-4) + (R,S)-2-chloropropionic acid (598-78-7) → camptothecin-20-O-2-chloropropionate (1112310-87-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	98.1%

(R,S)-2-chloropropionic acid (598-78-7) + iminodiacetic acid (142-73-4) → α-alanine-N-diacetic acid (22149-55-9)

Conditions	Yield
at 120℃; Temperature;	97%

(R,S)-2-chloropropionic acid (598-78-7) → 2-chloropropionyl chloride (7623-09-8)

Conditions	Yield
With thionyl chloride In hexane for 3h; Heating;	95%
With pyridine; phosgene at 55℃; for 1h; Reagent/catalyst; Temperature;	95.4%
With thionyl chloride In N,N-dimethyl-formamide at 85℃; for 2h;	85%

ethanol (64-17-5) + (R,S)-2-chloropropionic acid (598-78-7) → 2-chloro-propanoic acid, ethyl ester (535-13-7)

Conditions	Yield
With potassium chloride In tetrachloromethane at 72℃; for 4h; Kinetics; Rate constant; Thermodynamic data; activation energy, other temperatures (55, 63, 80 deg C);	95%
With sulfuric acid	85%
With hydrogenchloride

o-toluidine (95-53-4) + (R,S)-2-chloropropionic acid (598-78-7) → N-(2-methylphenyl)-2-chloropropanamide (19281-31-3)

Conditions	Yield
Stage #1: (R,S)-2-chloropropionic acid With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide for 0.25h; Stage #2: o-toluidine With 4-methyl-morpholine In water; N,N-dimethyl-formamide at 0 - 10℃; for 6.25h;	95%

tert-butyl 2-hydroxymethylacrylate (121065-74-5) + (R,S)-2-chloropropionic acid (598-78-7) → tert-butyl 2-((2-chloropropanoyloxy)methyl)acrylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1h;	93.4%
With dmap; dicyclohexyl-carbodiimide

2-methyl-3-sulfanylpropanoic acid (26473-47-2) + (R,S)-2-chloropropionic acid (598-78-7) → 2,5-dimethyl-3-thia-adipic acid (106014-16-8)

Conditions	Yield
Stage #1: 2-methyl-3-sulfanylpropanoic acid With sodium hydroxide In water at 20℃; for 0.166667h; Stage #2: (R,S)-2-chloropropionic acid In water for 2.5h;	93%

chloromethyl trimethyl benzene (51958-58-8) + N,N'-bis(glycidyl)-ethyleneurea (15336-78-4) + (R,S)-2-chloropropionic acid (598-78-7) → N,N'-bis(2-hydroxy-3-acryloyloxy-propyl)-ethyleneurea (422507-82-2)

Conditions	Yield
With triethylamine	92%

N1-(3-trifluoromethoxy-phenyl)-ethane-1,2-diamine (933717-56-7) + (R,S)-2-chloropropionic acid (598-78-7) → 2-chloro-N-[2-(3-trifluoromethoxy-phenylamino)-ethyl]-propionamide (1206600-53-4)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at -30℃;	92%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + (R,S)-2-chloropropionic acid (598-78-7) → 2-[(2-chloropropanoyl)oxy]tetralone (250652-65-4)

bis(tri-n-butyltin)oxide (56-35-9) + (R,S)-2-chloropropionic acid (598-78-7) → Tri-n-Butylzinn-2-chlorpropionat (33550-23-1)

Conditions	Yield
byproducts: H2O;	91%
byproducts: H2O;	91%

Benzimidazol-2-thiol (134469-07-1) + (R,S)-2-chloropropionic acid (598-78-7) → 2-(2-benzimidazolylthio)propionic acid (21547-70-6)

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Reflux;	91%

+ (R,S)-2-chloropropionic acid (598-78-7) → 2-[5-(4-Ethoxy-3,5-dimethoxy-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-propionic acid

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate Heating;	90%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + (R,S)-2-chloropropionic acid (598-78-7) → 2-(5-methoxy-1(3)H-benzimidazol-2-ylmercapto)-propionic acid (919467-09-7)

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Reflux;	90%

C93H188O47 + (R,S)-2-chloropropionic acid (598-78-7) → C96H191ClO48

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	90%

5-nitro-2-mercaptobenzimidazole (6325-91-3) + (R,S)-2-chloropropionic acid (598-78-7) → 2-(5-nitro-1(3)H-benzimidazol-2-ylmercapto)-propionic acid (114381-56-5)

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Reflux;	89%

(R,S)-2-chloropropionic acid (598-78-7) + 5-chloro-1H-benzoimidazole-2-thiol (25369-78-2) → 2-(5-chloro-1(3)H-benzimidazol-2-ylmercapto)-propionic acid (6963-77-5)

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Reflux;	89%

2,4-dichlorobenzenethiol (1122-41-4) + (R,S)-2-chloropropionic acid (598-78-7) → 2-(2,4-dichlorophenylsulfanyl)propionic acid (119424-79-2)

Conditions	Yield
With sodium thiophenolate; sodium hydroxide for 5h;	88.8%

3-(3,4-diossimetilenefenil)-4-ammino-5-mercapto-4H-1,2,4-triazolo (67572-54-7) + (R,S)-2-chloropropionic acid (598-78-7) → 2-(4-Amino-5-benzo[1,3]dioxol-5-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate Heating;	88%

4,4-diphenyl-2-cyclohexen-1-one (4528-64-7) + (R,S)-2-chloropropionic acid (598-78-7) → 4,4-diphenyl-6-(2-chloropropionyloxy)-cyclohex-2-en-1-one (295777-97-8)

Conditions	Yield
Stage #1: (R,S)-2-chloropropionic acid With manganese triacetate In benzene for 2.5h; Substitution; Heating; Stage #2: 4,4-diphenyl-2-cyclohexen-1-one In benzene for 20h; Oxidation; Heating;	88%

Upstream product

• 849585-22-4 LACTIC ACID 
• 3156-70-5 1-Nitropropen 
• 16714-77-5 1,3-dichlorobutan-2-one 
• 78-97-7 2-hydroxy-propionitrile 
• 1617-17-0 2-chlorpropionitrile 
• 7790-94-5 chlorosulfonic acid 
• 802294-64-0 propionic acid 
• 7719-12-2 phosphorus trichloride 
• 79-03-8 propionyl chloride 
• 7647-01-0 hydrogenchloride 
• 7782-50-5 chlorine 
• 56-23-5 tetrachloromethane 
• 64-19-7 acetic acid 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 104640-54-2 S-((Ξ)-1-carboxy-ethyl)-L-cysteine 
• 68797-46-6 2-chloro-propionic acid-(2-butoxy-ethyl ester) 
• 5434-63-9 9,10-dihydro-9,10-ethanoanthracene-11-carboxylic acid 
• 56674-68-1 2-(cyclohexyloxy)propanoic acid 
• 7623-09-8 2-chloropropionyl chloride 
• 565-64-0 2,3-dichloropropanoic acid 
• 75-99-0 2,2-Dichloropropionic acid 
• 79-42-5 2-mercaptopropanoic acid 
• 79-10-7 acrylic acid 
• 2274-50-2 phenylalanine-o-carboxylic acid 
• 19275-82-2 2-(1-chloroethyl)-1H-benzo[d]imidazole 
• 40058-87-5 iso-propyl-2-chloropropanoate 
• 120-36-5 2-(2,4-dichlorophenoxy)propionic acid 

Relevant articles and documents

Promotive effects in α-monochloropropionic acid catalytic synthesis with propionic anhydride

Selective α-chlorination of propionic acid to synthesize α-monochloropropionic acid was investigated in a laboratory-scale at 130 °C at atmospheric total pressure and in the presence of propionic anhydride as catalyst. Sulfuric acid and common Lewis acid were selected as promotive catalysts considering that the acid-catalyzed enolization is the rate determining step in the chlorination reaction of this experiment, also the reaction selectivity and activity were discussed in the presence of promotive catalysts. The studies revealed that the ferric chloride and sulfuric acid all have prominent promotive effects. Typically the amount of α- monochloropropionic acid can reach 96.14 % when 0.07 g of ferric chloride was added. Furthermore, our results demonstrated that the reaction selectivity and activity were dramatically enhanced after introducing Lewis acid as promotive catalysts.

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