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122-11-2

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122-11-2 Usage

Brand Name(s) in US

Albon, Bactrovet, and generic

Chemical Properties

White Solid

Originator

Madribon,Roche,US,1958

Uses

Different sources of media describe the Uses of 122-11-2 differently. You can refer to the following data:
1. Antibacterial.
2. Antibacterial.This compound is a contaminant of emerging concern (CECs).

Definition

ChEBI: A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.

Manufacturing Process

1.4 g of 4-phenylsulfonyl-2,6-dimethoxypyrimidine and 4 g of sodium sulfanilamide (both dried over potassium hydroxide) were very finely ground and heated in an oil bath for 10 hours at 120°C (inside temperature). The reaction mixture was taken up in 30 ml of water and treated with 3 ml of 2 N sodium hydroxide solution. After standing for one hour at 0°C, the turbid solution was filtered and the filtrate was made alkaline with sodium carbonate. After again standing for one hour at 0°C, the precipitate was filtered off (1.9 g of regenerated sulfanilamide) and the filtrate was neutralized with acetic acid, whereupon crystallization resulted. The isolated crystals of 4-sulfanilamido- 2,6-dimethoxypyrimidine weighed 1.3 g (84% of theory), melting point 190°C to 196°C.

Therapeutic Function

Antibacterial

Pharmaceutical Applications

2,4-Dimethoxy-6-sulfanilamido-1,3-diazine. A rapidly absorbed compound with a long half-life (38–40 h) and a high degree of protein binding (98%). Renal clearance is very slow, and daily dosage maintains adequate plasma levels.

Safety Profile

Moderately toxic by intraperitoneal, intravenous, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.

Veterinary Drugs and Treatments

Sulfadimethoxine injection and tablets are approved for use in dogs and cats for respiratory, genitourinary, enteric and soft tissue infections caused by susceptible organisms. Sulfadimethoxine is used in the treatment of coccidiosis in dogs although not approved for this indication. In horses, sulfadimethoxine injection is approved for the treatment of respiratory infections caused by Streptococcus equi. In cattle, the drug is approved for treating shipping fever complex, calf diphtheria, bacterial pneumonia and foot rot caused by susceptible organisms. In poultry, sulfadimethoxine is added to drinking water to treat coccidiosis, fowl cholera, and infectious coryza.

Check Digit Verification of cas no

The CAS Registry Mumber 122-11-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 122-11:
(5*1)+(4*2)+(3*2)+(2*1)+(1*1)=22
22 % 10 = 2
So 122-11-2 is a valid CAS Registry Number.

122-11-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (S0359)  Sulfadimethoxine  >98.0%(HPLC)(T)

  • 122-11-2

  • 25g

  • 950.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001677)  Sulfadimethoxine  European Pharmacopoeia (EP) Reference Standard

  • 122-11-2

  • Y0001677

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001679)  Sulfadimethoxine for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 122-11-2

  • Y0001679

  • 1,880.19CNY

  • Detail
  • USP

  • (1626001)  Sulfadimethoxine  United States Pharmacopeia (USP) Reference Standard

  • 122-11-2

  • 1626001-200MG

  • 4,662.45CNY

  • Detail
  • Sigma-Aldrich

  • (S7007)  Sulfadimethoxine  analytical standard, ≥98.5% (TLC)

  • 122-11-2

  • S7007-10G

  • 491.40CNY

  • Detail
  • Sigma-Aldrich

  • (S7007)  Sulfadimethoxine  analytical standard, ≥98.5% (TLC)

  • 122-11-2

  • S7007-25G

  • 1,188.72CNY

  • Detail
  • Sigma-Aldrich

  • (S7007)  Sulfadimethoxine  analytical standard, ≥98.5% (TLC)

  • 122-11-2

  • S7007-100G

  • 3,230.37CNY

  • Detail
  • Sigma-Aldrich

  • (46794)  Sulfadimethoxine  VETRANAL, analytical standard

  • 122-11-2

  • 46794-250MG

  • 404.82CNY

  • Detail

122-11-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name sulfadimethoxine

1.2 Other means of identification

Product number -
Other names 4-Amino-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:122-11-2 SDS

122-11-2Synthetic route

4-p-acetamidobenzenesulfonamido-2,6-dimethoxypyrimidine
555-25-9

4-p-acetamidobenzenesulfonamido-2,6-dimethoxypyrimidine

sulfadimethoxine
122-11-2

sulfadimethoxine

Conditions
ConditionsYield
With methanol; sodium hydroxide at 85℃; for 6h; Temperature; Large scale;96%
With sodium hydroxide
N-(2,6-dimethoxy-pyrimidin-4-yl)-4-nitro-benzenesulfonamide
37063-70-0

N-(2,6-dimethoxy-pyrimidin-4-yl)-4-nitro-benzenesulfonamide

sulfadimethoxine
122-11-2

sulfadimethoxine

Conditions
ConditionsYield
With iron; ammonium chloride In water for 10h; Heating;81.3%
Trimethyl-4-(2,6-dimethoxypyrimidinyl)ammoniumchlorid
77767-96-5

Trimethyl-4-(2,6-dimethoxypyrimidinyl)ammoniumchlorid

sodium-salt of sulfanilamide

sodium-salt of sulfanilamide

sulfadimethoxine
122-11-2

sulfadimethoxine

Conditions
ConditionsYield
With acetamide
4-nitrobenzenediazonium chloride
100-05-0

4-nitrobenzenediazonium chloride

benzothiophen-3-yl-glyoxal phenylhydrazone

benzothiophen-3-yl-glyoxal phenylhydrazone

sulfadimethoxine
122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SO2 / CuSO4 / acetic acid / 6 - 20 °C
2: 84.2 percent / pyridine / 2 h / 56 - 58 °C
3: 81.3 percent / Fe, NH4Cl / H2O / 10 h / Heating
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

(+-)-2-amino-5-butyl-thiazol-4-one

(+-)-2-amino-5-butyl-thiazol-4-one

sulfadimethoxine
122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84.2 percent / pyridine / 2 h / 56 - 58 °C
2: 81.3 percent / Fe, NH4Cl / H2O / 10 h / Heating
View Scheme
2,6-dimethoxypyrimidin-4-amine
3289-50-7

2,6-dimethoxypyrimidin-4-amine

sulfadimethoxine
122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aqueous NaOH
View Scheme
p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfadimethoxine
122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aqueous NaOH
View Scheme
sulfadimethoxine
122-11-2

sulfadimethoxine

2,3-isopropylidene-glyceraldehyde
15186-48-8

2,3-isopropylidene-glyceraldehyde

N-(2,6-dimethoxypyrimidin-4-yl)-4-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}amino)benzenesulfonamide

N-(2,6-dimethoxypyrimidin-4-yl)-4-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}amino)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dimethyl sulfoxide; toluene Condensation;100%
sulfadimethoxine
122-11-2

sulfadimethoxine

Methacryloyl chloride
920-46-7

Methacryloyl chloride

sulfadimethoxine methacrylamide

sulfadimethoxine methacrylamide

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 20℃; for 1.5h; Cooling with ice;97%
With sodium hydroxide In acetone at 20℃; for 12h;96.2%
With sodium hydroxide In water; acetone at 0℃;85%
With sodium hydroxide In acetone at 0℃;
sulfadimethoxine
122-11-2

sulfadimethoxine

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

cyclohexyltrifluoro-λ4-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

methyl 4-(cyclohexyl((4-(N-(2,6-dimethoxypyrimidin-4-yl)sulfamoyl)phenyl)amino)methyl)benzoate

methyl 4-(cyclohexyl((4-(N-(2,6-dimethoxypyrimidin-4-yl)sulfamoyl)phenyl)amino)methyl)benzoate

Conditions
ConditionsYield
With sodium hydrogen sulfate; Ir(dF(CF3)ppy)2(bpy)PF6 In 1,4-dioxane at 24℃; for 24h; Petasis Reaction; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;97%
sulfadimethoxine
122-11-2

sulfadimethoxine

silver nitrate

silver nitrate

C12H13AgN4O4S

C12H13AgN4O4S

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 1h;95%
In methanol; water for 3h;
sulfadimethoxine
122-11-2

sulfadimethoxine

C12H12(2)H2N4O4S

C12H12(2)H2N4O4S

Conditions
ConditionsYield
With water-d2 In tetrahydrofuran at 80℃; under 760.051 Torr; for 3h; Sealed tube;95%
sulfadimethoxine
122-11-2

sulfadimethoxine

2,4,6-triphenylpyrilium perchlorate
1484-88-4

2,4,6-triphenylpyrilium perchlorate

1-[4-(2,6-Dimethoxy-pyrimidin-4-ylsulfamoyl)-phenyl]-2,4,6-triphenyl-pyridinium; perchlorate

1-[4-(2,6-Dimethoxy-pyrimidin-4-ylsulfamoyl)-phenyl]-2,4,6-triphenyl-pyridinium; perchlorate

Conditions
ConditionsYield
In acetic acid for 2h; Heating;94%
2-chloromethyl-1H-benzimidazole
4857-04-9

2-chloromethyl-1H-benzimidazole

sulfadimethoxine
122-11-2

sulfadimethoxine

4-[(1H-Benzoimidazol-2-ylmethyl)-amino]-N-(2,6-dimethoxy-pyrimidin-4-yl)-benzenesulfonamide
107090-14-2

4-[(1H-Benzoimidazol-2-ylmethyl)-amino]-N-(2,6-dimethoxy-pyrimidin-4-yl)-benzenesulfonamide

Conditions
ConditionsYield
In methanol for 4h; Heating;88%
sulfadimethoxine
122-11-2

sulfadimethoxine

mercury(II) diacetate
1600-27-7

mercury(II) diacetate

Hg(sulfadimethoxinato)2

Hg(sulfadimethoxinato)2

Conditions
ConditionsYield
In methanol Hg(II) acetate in methanol added dropwise with stirring; stirred (18 h,room temp.); filtered off; dried; elem. anal.;87%

122-11-2Downstream Products

122-11-2Related news

Sulfadimethoxine (cas 122-11-2) and sulfaguanidine: Their sorption potential on natural soils09/24/2019

Sulfonamides (SAs) are one of the oldest groups of veterinary chemotherapeutic agents. As these compounds are not completely metabolized in animals, a high proportion of the native form is excreted in feces and urine. They are therefore released either directly to the environment in aquacultures...detailed

An amperometric aptasensor for ultrasensitive detection of Sulfadimethoxine (cas 122-11-2) based on exonuclease-assisted target recycling and new signal tracer for amplification09/09/2019

The risks caused by veterinary drug residues in animal foodstuffs are of great concern to the public. Accordingly, this work reported an amperometric aptasensor for highly sensitive detection of sulfadimethoxine (SDM). Functionalised fullerene (C60)-doped graphene (C60-rGO) nanohybrid was design...detailed

Degradation of Sulfadimethoxine (cas 122-11-2) by permanganate in aquatic environment: Influence factors, intermediate products and theoretical study09/07/2019

The excess sulfadimethoxine (SDM) in the environment could lead to antibiotic resistance by microorganisms and may do harm to many aquatic organisms. In this work, the removal of SDM by potassium permanganate (KMnO4) was comprehensively studied. The influence of various factors, including the pH...detailed

Original Research ArticleDetection of Sulfadimethoxine (cas 122-11-2) in meat samples using a novel electrochemical biosensor as a rapid analysis method09/05/2019

In this work, an electrochemical aptamer-based biosensor was fabricated on a pencil graphite electrode (PGE). The bare PGE was modified with a nanocomposite including reduced graphene oxide (RGO) and Au nanoparticles for sulfadimethoxine (SDM) determination. In order to fabricate the electrode i...detailed

Electrochemical aptasensor for Sulfadimethoxine (cas 122-11-2) detection based on the triggered cleavage activity of nuclease P1 by aptamer-target complex09/04/2019

Herein, a simple and selective electrochemical method was developed for sulfadimethoxine detection based on the triggered cleavage activity of nuclease P1 by the formation of aptamer and sulfadimethoxine conjugate. After probe DNA was immobilized on gold electrode surface, aptamer DNA labeled wi...detailed

122-11-2Relevant articles and documents

A sulfonamide - 2, 6 - dimethoxy pyrimidine preparation method (by machine translation)

-

Paragraph 0027; 0028; 0035; 0036; 0040; 0041; 0045; 0046, (2017/12/05)

The invention relates to a sulfonamide - 2, 6 - dimethoxy pyrimidine of the preparation method, the 4 - amino - 2, 6 - dimethoxy pyrimidine and P-acetyl amino sulfonyl chloride in N, N - dimethyl formamide and the presence of triethylamine, in the 15 - 20 °C reaction under 10 - 14 hours, then post-processed to obtain 4 - P-acetyl amino sulfonamide - 2, 6 - dimethoxy pyrimidine; will be 4 - P-acetyl amino sulfonamide - 2, 6 - dimethoxy pyrimidine in methanol and the mass concentration is 15% -25% of sodium hydroxide solution in the presence of, in 85 - 90 °C reaction 5 - 7 hours, then post-processed to obtain the sulfonamide - 2, 6 - dimethoxy pyrimidine. The invention the synthetic route and the optimization of the process conditions and the like, so that the realization of the kg sulfonamide - 2, 6 - dimethoxy pyrimidine at the time of preparation, sulfonamide - 2, 6 - dimethoxy pyrimidine yield and purity of the still very high, is suitable for industrial production. (by machine translation)

p-NITROBENZENESULFONYL CHLORIDE AS A RAW MATERIAL FOR THE MANUFACTURE OF SULFANILAMIDE PREPARATIONS

Luk'yanov, A. V.,Onoprienko, V. S.,Borodina, K. S.,Zasosov, V. A.,Van'kovich, E. V.,et al.

, p. 640 - 644 (2007/10/02)

-

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