[ CAS No. 5551-12-2 ]

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CAS No. 5551-12-2, is an aryls compound, with a molecular weight of 230.02, molecular formula C7H4BrNO3, Ambeed provides reports for batches of (such as NMR, HPLC/GC).

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Product Details

CAS No. :5551-12-2MDL No. :MFCD00463687
Formula :C7H4BrNO3InChI Key :GSXUXSXBEUJRAJ-UHFFFAOYSA-N
M.W :230.02Pubchem ID :608099
Boiling Point :334.4буC at 760 mmHg
Synonyms :

Computed Properties

TPSA : 62.9 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 1

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 5551-12-2 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 60956-26-5 ]
  • [ 5551-12-2 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: at 0 - 10℃; for 1.00 h;
Stage #2: With sodium carbonate In water
Stage #3: With hydrogenchloride; water In ethanol for 0.75 h;
[000194] Step A: To a solution of 4-bromo-l-methyl-2-nitrobenzene (300 g, 1.38 mol) in acetic anhydride (2400 mL) at 0 °C, was added slowly concentrated sulfuric acid (324 ml), followed by a solution of chromium tri oxide (384 g, 3.84 mole) in acetic anhydride (2160 ml).The internal temperature was controlled below 10 °C. After stirring for lh, the contents in the flask were poured into a mixture of ice and water. The solid was filtered and washed with water until the washings were colorless. The product was suspended in 1800 ml of 2percent aqueous sodium carbonate solution with stirring. After thorough mixing, the solid was filtered and washed with water and dried under reduced pressure.[000195] A suspension of the diacetate in a mixture of 1360 ml of concentrated hydrochloric acid, 1250 ml of water, and 480 ml of ethanol was refluxed for 45 minutes. The mixture was then cooled to room temperature and the solid was filtered and washed with water. 4-bromo-2- nitrobenzaldehyde (147 g, 45percent for two steps) was afforded as a brown solid without further purification.
Reference: [1] Patent: WO2012/97177, 2012, A2. Location in patent: Page/Page column 57-58
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2462 - 2467
[3] Organic Preparations and Procedures International, 2006, vol. 38, # 3, p. 325 - 331
[4] Synthetic Communications, 2001, vol. 31, # 23, p. 3721 - 3727
[5] Heterocycles, 1994, vol. 39, # 2, p. 767 - 778
[6] Journal of the Chemical Society, 1945, p. 167
[7] Journal fuer Praktische Chemie (Leipzig), 1935, vol. <2> 142, p. 35
[8] Patent: WO2011/22509, 2011, A2
[9] Patent: WO2011/22508, 2011, A2
[10] Patent: WO2011/22508, 2011, A2
[11] Patent: WO2011/22509, 2011, A2
[12] Patent: WO2012/97177, 2012, A2
[13] Patent: WO2016/96778, 2016, A1
[14] Patent: WO2017/46112, 2017, A1
  • 2
  • [ 22996-19-6 ]
  • [ 5551-12-2 ]
YieldReaction ConditionsOperation in experiment
78% With manganese(IV) oxide In dichloromethane at 20℃; for 12.00 h; Step 2. 4-Bromo-2-nitrobenzaldehydeManganese (IV) oxide (4eq) was added to a 0.18M solution of (4-bromo-2-nitrophenyl)methanol in dichloromethane. The suspension was stirred at ambient temperature under Argon for 12 h. The reaction mixture was filtered through celite and filter cake was washed with dichloromethane. The combined filtrate was concentrated to give brown color solid in 78percent yield.
Reference: [1] Patent: WO2007/117607, 2007, A2. Location in patent: Page/Page column 333
  • 3
  • [ 135308-80-4 ]
  • [ 5551-12-2 ]
Reference: [1] Synthetic Communications, 2001, vol. 31, # 23, p. 3721 - 3727
[2] Journal of the Chemical Society, 1945, p. 167
[3] Patent: WO2004/81008, 2004, A1. Location in patent: Page 116
[4] Patent: WO2011/22509, 2011, A2. Location in patent: Page/Page column 57-58
[5] Patent: WO2011/22508, 2011, A2. Location in patent: Page/Page column 50; 51
  • 4
  • [ 3460-18-2 ]
  • [ 68-12-2 ]
  • [ 5551-12-2 ]
Reference: [1] Chemische Berichte, 1989, vol. 122, p. 1199 - 1202
[2] Patent: US2004/116422, 2004, A1. Location in patent: Page/Page column 30-31
  • 5
  • [ 99474-21-2 ]
  • [ 5551-12-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2462 - 2467
[2] Patent: WO2007/24612, 2007, A2. Location in patent: Page/Page column 35; 3/3
  • 6
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
YieldReaction ConditionsOperation in experiment
24% at 25℃; for 3.00 h; Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 7
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
21% at 25℃; for 3.00 h; N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 8
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
10% at 60℃; for 3.00 h; Treatment of 1 (459 mg, 3.03 mmol) and NBS (677 mg, 3.80 mmol) in H2SO4 (3.0 mL) at 60 oC as described above afforded the following fractions in order of elution: (I) 7 (21 mg, 0.07 mmol, 2percent); (II) 2 (66 mg, 9percent) and 4 (24 mg, 3percent); (III): 2 (5 mg, 0.7percent) and 3,4-dibromo-2-nitrobenzaldehyde 6 (85 mg, 9percent); (IV) 5 (59 mg, 8percent), 8 (13 mg, 1percent), and 1 (18 mg, 4percent); (V) 3 (20 mg, 0.09 mmol, 3percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 9
  • [ 552-89-6 ]
  • [ 882772-99-8 ]
  • [ 5551-12-2 ]
  • [ 56990-05-7 ]
  • [ 20357-20-4 ]
  • [ 20357-21-5 ]
  • [ 1559060-83-1 ]
YieldReaction ConditionsOperation in experiment
20% at 25℃; for 3.00 h; Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 954 - 958
  • 10
  • [ 552-89-6 ]
  • [ 5551-12-2 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
  • 11
  • [ 82420-34-6 ]
  • [ 5551-12-2 ]
Reference: [1] Heterocycles, 1994, vol. 39, # 2, p. 767 - 778
  • 12
  • [ 78508-22-2 ]
  • [ 5551-12-2 ]
Reference: [1] Organic Preparations and Procedures International, 2006, vol. 38, # 3, p. 325 - 331
  • 13
  • [ 3460-18-2 ]
  • [ 5551-12-2 ]
Reference: [1] Patent: EP1182195, 2002, A1. Location in patent: Example 67
  • 14
  • [ 408526-96-5 ]
  • [ 5551-12-2 ]
Reference: [1] Molecules, 2010, vol. 15, # 8, p. 5561 - 5580
  • 15
  • [ 959089-98-6 ]
  • [ 5551-12-2 ]
Reference: [1] Patent: DE149748,
[2] Chemische Berichte, 1904, vol. 37, p. 1873
[3] Chemische Berichte, 1903, vol. 36, p. 3301
[4] Patent: DE149749,
  • 16
  • [ 99277-71-1 ]
  • [ 5551-12-2 ]
Reference: [1] Patent: WO2007/117607, 2007, A2
  • 17
  • [ 119-32-4 ]
  • [ 5551-12-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1935, vol. <2> 142, p. 35
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